
Hosted by Walter Thompson · EN

In this episode, I’m joined by Jon Callaghan, co-founder and managing partner at True Ventures, and Julie Bornstein — CEO and co-founder of Daydream, founder of The Yes, and former COO of Stitch Fix — to break down what investors really evaluate in the first 18 months of a company’s life. Drawing from their shared history as investor and founder, we talk candidly about runway, hiring before certainty exists, conviction versus ego, and how trust between founders and investors gets tested when plans change. Julie explains how she approached budgeting and milestones for The Yes as a non-technical founder, while Jon shares how early-stage investors assess learning, decision-making, and leadership long after the pitch meeting ends. RUNTIME 50:28 EPISODE BREAKDOWN (2:43) Jon: “Julie and I met in graduate school.” (4:24) Julie chose a different VC firm for her first seed round at The Yes (10:33) How would Jon have assessed The Yes if he didn’t know Julie? (13:14) Julie: “Runway is your best friend and your biggest gift.” (14:59) How non-technical founders can sketch out a financial model (22:37) Jon: “There’s an immense river of goodness that flows underneath Silicon Valley.” (25:30) How did True Ventures size up SAM for The Yes? (29:00) Only work with engineers who understand your problem (31:25) Some of Jon’s post-check expectations for founders (41:44) What are some questions founders should ask VCs in their first meeting? (45:42) One experiment a pre-seed/seed-stage founder can try next week (48:14) The final question LINKS Julie Bornstein Jon Callaghan True Ventures Daydream Top e-commerce veteran Julie Bornstein unveils Daydream—an AI-powered shopping agent that’s 25 years in the making, Forbes, 6/25/2025 Pinterest to Acquire THE YES, an AI Powered Shopping Platform for Fashion, press release, 6/2/2022 StitchFix SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw Thanks for listening! – Walter

For years, founders have been told to build a defensible moat. But in AI, where platforms, models, and capabilities can shift overnight, that advice is starting to feel outdated. In this episode of Fund/Build/Scale, Simular CEO and co-founder Ang Li talks about what it actually means to build a company when the underlying technology won’t sit still. Rather than evangelizing agents or predicting the future of work, Ang gets unusually candid about fragility, speed, judgment, and how founders should think when technical advantages may be temporary by default. The conversation digs into small-team execution, founder productivity, decision-making under uncertainty, and the uncomfortable question many AI founders avoid: what if the next platform update eats your product? Note: This interview was recorded before Simular closed its $21.5M Series A in December 2025. RUNTIME 56:44 EPISODE BREAKDOWN (1:52) What is Simular, and how does it work? (6:11) How Ang and co-founder Jiachen Yang connected (9:00) How much time passed between Day Zero and serving their first customer? (13:54) The moment Ang realized " this is gonna be like something huge." (17:21) How he approaches founder-led sales and what he looks for in a GTM hire (26:34) Maintaining cohesion when you're leading a distributed team (32:23) Should you hire a new employee, or build a new agent? (34:50) Why Ang made talking AI gorillas part of Simular's GTM strategy (38:20)"If everyone becomes too cautious there, that actually prevents the innovation part." (43:55) "There's never a moat on anything." (51:16) The final question LINKS Ang Li Jiachen Yang Simular Meet the AI Agent with Multiple Personalities, Wired, 4/16/2025 Simular Raises $21.5M to Build Autonomous Computer Agents, 12/2/2025 What is Robotic Process Automation (RPA)?, IBM SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw Thanks for listening! – Walter.

When most founders look at markets dominated by Google or Apple, they see a dead end. Ariel Seidman saw an opening. Before founding Hivemapper, Ariel helped scale Yahoo Maps during a period when search and mapping were rapidly evolving. That experience gave him a front-row seat to how large-scale mapping systems are built — and how technical, capital, and organizational constraints shape the pace of innovation at scale. In this episode, he breaks down what it really takes to build a startup against giants: why data moats matter more than UI, how to layer products instead of attacking incumbents head-on, and how insider knowledge can become an unfair advantage — if you’re willing to unlearn Big Tech habits that don’t translate to startups. We also dig into Hivemapper’s decentralized approach to mapping, the role of physical AI and real-world data, the tradeoffs behind crypto incentives, and why the future of maps looks more like a spatial intelligence platform than a navigation app. If you’re thinking about taking what you’ve learned inside Big Tech and applying it to your own startup, this is a conversation you’ll want to hear. RUNTIME 46:57 EPISODE BREAKDOWN (2:11) What is Hivemapper? (6:34) Scaling Yahoo Maps: Lessons from an Early Market Leader (9:04) Why Capital and Infrastructure Matter More Than Design (11:49) From Insider to Founder: Deciding to Build Again (15:00) Customer Discovery at Scale: Coverage, Accuracy, and the Long Tail (19:10) Beyond Navigation: Maps as a Spatial Intelligence Platform (22:46) Big Tech vs. Startups: Some Skills Transfer — and Some Don't (27:31) Building Against Giants by Building One Layer at a Time (31:39) Creating a Double Flywheel (and Making it Spin) (45:10) The Final Question LINKS Ariel Seidman Hivemapper Beemaps Hivemapper network blog Hivemapper Raises $18M From Multicoin Capital to Create the World’s First Decentralized Mapping Network, 4/5/2022 Bee Maps, Powered by Hivemapper, Raises $32 Million to Scale the Next Generation of AI-Powered Mapping, 10/6/2025 SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw Thanks for listening! – Walter.

Odille Sánchez leads the Tech and Scientific-Based Entrepreneurship Center of Excellence at Tecnológico de Monterrey, where she works with hundreds of early-stage founders across Latin America. In this episode, she explains how mindset, methodology, and community are reshaping what it means to launch a startup in a region where early capital is scarce and institutional support is fragmented. We also talk about: Why resource orchestration — not acceleration — is what most founders need How cultural attitudes toward risk impact founder behavior What Latin American investors and institutions can learn from each other Why commercialization is often the missing piece How to help first-time founders develop a global mindset from day one Whether you're supporting under-networked founders or trying to build in an emerging market, Odille offers a clear-eyed look at what it really takes to go from scarcity to scale. RUNTIME 37:46 EPISODE BREAKDOWN [2:10] Mission-Driven Work at Tecnológico de Monterrey [5:20] Resource Orchestration, Not Acceleration [6:45] " We work with a lot of profiles." [8:47] Bridging The Cultural Gap Around Risk-Taking [11:37] A Founder Success Story: Ricardo Baez + Safe Fruit [14:06] What to Do When You Don’t Have a Network [17:06] The Disconnect Between Capital and Opportunity [20:42] How Latin American Founders Can Engage Global Angel Investors [23:02] The Missing Skillset: Commercialization [30:08] What Silicon Valley Advice Doesn’t Translate [34:43] Odille’s Parting Advice for Outsiders LINKS Odille Sánchez Centro de Prensa dl Tecnológico de Monterrey Shaping Innovation and Entrepreneurship Ecoystems: An Outcome-based Model From reflection to intention: Rethinking how we build startups and innovation ecosystems SUBSCRIBE 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw Thanks for listening! – Walter.

When you don’t have generational wealth or a built-in network, the startup path isn’t just harder — it’s different. In this episode, I’m joined by James Norman and Sean Green of Black Operator Ventures for a candid conversation about what early-stage founders actually need to understand to raise capital and scale companies when they’re coming from the outside. We talk about why fundraising is a power-dynamic game, not a meritocracy — and why underrepresented founders have to master the theater of venture capital without losing themselves in the process. James and Sean also break down what they look for when leading seed rounds, why warm intros function as the first real filter, and how founders can manufacture momentum even without friends-and-family money. This conversation goes deep on: How to position yourself when you don’t start at the same starting line The difference between venture-scale companies and businesses that shouldn’t chase VC Why execution, storytelling, and follow-up matter more than polish How to turn cold outreach into real human capital Why Black founders are uniquely positioned to exploit the current AI moment If you’re an underrepresented founder trying to de-risk your leap, get into the right rooms, or understand why the rules feel unwritten — this conversation names the rules out loud. RUNTIME 54:24 EPISODE BREAKDOWN (1:52) What motivated Sean and James to start Black Operator Ventures (6:51) Where are they looking for opportunities? (8:27) Top priority: Founders building real-world solutions with few regulatory hurdles (11:44) Why obtaining a warm intro to a VC is a founder's first test (15:20) Fundraising is theater: Study the audience to learn your role (22:29) Red flags first-time founders should avoid waving (27:00) Tactical advice for aspiring founders who still work full-time jobs (30:24) “ It doesn't seem risky because we're betting on ourselves, and we believe we can do anything.” (34:38) How to find out if you should bootstrap or find a VC (38:30) Which signals tell Sean and James a founder is ready for a check (41:55) Why founders still need to spend some time in Silicon Valley (46:02) Black founders can " 10x ourselves with AI in ways that other people can't." (48:32) One action you can take this week to extend your network LINKS James Norman Sean Green Black Operator Ventures Q2 2025 Black Venture Funding Report, HBCUvc Share Of Startup Funding For Black Founders Hits Multiyear Low, Crunchbase The State of U.S. Household Wealth, Federal Reserve Bank of St. Louis Three in Ten Black Americans Over Age 25 Hold a Bachelor’s Degree, The Journal of Blacks in Higher Education SUBSCRIBE 📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw 📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/ 📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/ Thanks for listening! – Walter.

Building a startup in Africa isn’t the same as doing it in Silicon Valley. Some challenges overlap, but many don’t, like currency volatility, limited early-stage funding, and investors who expect you to scale faster than the market allows. So how do you grow beyond your home market? How do you raise funds when VC is scarce? And what do African founders need to do to make their startups more venture-backable? To find out, I spoke with Mobola da-Silva, a partner at Capria Ventures who’s based in Nairobi, Kenya. She’s been investing in Africa and other emerging markets for nearly two decades and knows exactly what separates startups that thrive from those that stall. She shares practical insights on navigating currency risk, securing funding, and preparing for Series A — even if you don’t have a deep-pocketed network to lean on. If you’re an African founder trying to build a company that investors take seriously, this episode is for you. RUNTIME 46:19 EPISODE BREAKDOWN (2:03) How Mobola got her start in VC and the path that led her to Capria Ventures. (4:09) Capria Ventures' investment thesis. (5:32) The regions and sectors where generative AI is creating real value. (10:41) The best way to pitch Capria Ventures — and what investors want to see. (12:26) “A venture-backable business has to be able to achieve significant scale.” (15:13) “We're getting a bit more creative in Africa around funding for startups.” (16:20) How currency volatility impacts valuations — and strategies for mitigating risk. (22:18) “To pitch successfully, you have to be able to tell a story, right?” (23:51) Why Capria Ventures avoids solo founders and what investors look for in teams. (28:33) “Many investors don't think of product-market fit as a binary thing.” (31:29) The key metrics that signal true product-market fit. (33:49) “Make sure that you have a strong business before you try to start to move it to another market.” (37:49) “Silicon Valley looms larger than life in Africa.” How founders should interpret this influence. (42:46) Mobola’s top advice for early-stage founders in Africa looking to scale and raise capital. LINKS Mobola da-Silva Capria Ventures Investment inquiries SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Eric Ly is the CEO of KarmaCheck, where he’s tackling a problem he first noticed years ago as a co-founder of LinkedIn: People don’t always tell the truth about themselves. To address this, KarmaCheck — launched in 2019 — automates key aspects of the background check process. By reducing complexity, employers can speed up hiring, while job applicants experience less friction along the way. “This is one of the first touch points with the employer: experiencing pain and frustration having to go through this process,” said Eric. “For us to show up with something new and different and better was frankly a breath of fresh air for the employers, the customers that we work with.” In this episode, we discuss: Jumping into a highly regulated industry with no prior domain expertise Why customer discovery should focus on patterns, not one-off insights The benefits of selling new features before they exist How to balance customer requests without losing focus We also talk about stepping out of LinkedIn’s shadow, resisting the temptation to build for a single customer, and knowing when to say “no” to feature requests. RUNTIME 40:20 EPISODE BREAKDOWN (1:37) “Several years ago, I became really interested in this whole concept around trust and trust online.” — How Eric first recognized the problem that led to KarmaCheck. (3:22) Entering a highly regulated industry without prior experience — where Eric found the confidence to take the leap. (5:30) A look back at KarmaCheck’s first hires — who they brought in early and why. (6:47) How KarmaCheck convinced early customers to take a chance on an unproven solution. (10:36) “Where employers don't even meet the people that they interview in person, there's an opportunity for the wrong things to happen.” (12:21) “We identified a pain point in corporate America that people often experience frustration with.” (14:34) How Eric used early customer feedback to shape KarmaCheck’s product strategy. (16:11) The role of proof-of-concept programs in building customer trust. (21:16) “Make sure that whatever you commit to in your product is going to be applicable for more than one customer.” (24:47) When customer feedback leads you down the wrong path — how to recognize it and recover. (27:46) Why it’s important to keep track of rejected product ideas. (29:49) The lessons from LinkedIn that Eric chose not to apply at KarmaCheck. (32:54) Advice for founders who want to step out of a shadow and build something completely new. (35:54) How to find a mentor when you don’t have a built-in network — Eric’s tips for making meaningful connections. (38:24) The one question Eric would ask a CEO if he were interviewing for a job at an early-stage startup. LINKS KarmaCheck Eric Ly KarmaCheck Raises $45 Million Series B to Modernize Background Checks and Credentialing (Press release. 6/27/2024) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Most early-stage founders I talk to are focused on getting their first customers, hiring their first employees, or maybe, if they’re lucky, closing their first round of funding. But what happens after that? For Rohit Choudhary, the answer was building a whole new category. Rohit is the CEO and co-founder of Acceldata, a data observability platform that helps companies manage the complexity of modern data infrastructure. Before starting the company, he spent years inside the problem — working on data engineering challenges at Hortonworks and other enterprise tech firms. Like a lot of technical founders, Rohit didn’t start out dreaming of being a CEO — but the problem was too big to ignore. In this episode, we talk about: Why data engineering lacked the right tooling and how that led to Acceldata How his team validated the concept with real-world customer pain points The trade-offs of building in stealth mode vs. in public What he’s learned about hiring, scaling, and making the leap from engineer to CEO If you’re trying to figure out how to go from technical insight to scalable business, this one’s for you. RUNTIME 37:37 EPISODE BREAKDOWN (2:16) “ There are four of us co-founders, and we were all part of the same engineering team at Hortonworks.” (4:33) “ We felt that here was a unique opportunity for us to be able to build something really, really large and big.” (6:16) How Acceldata approached proof-of-concept programs in its early days. (8:23) “ How did you decide which one of you would become the CEO?” (11:31) Rohit’s seed-stage recruiting strategy: “ we had to excite them with the long-term vision.” (14:35) “ People like me, we learned how to sell despite coming from an engineering background.” (16:46) Why the co-founders “took a leap of faith” by formalizing their sales process early. (18:46) “ We were familiar with how business is conducted in the U.S.,” which made expansion easier. (21:08) Early challenges they faced after closing a Series A. (23:08) How “a big mistake” from a previous startup still influences Rohit’s choices today. (25:30) Wondering if it’s time to throw in the towel? Do a self-assessment. (28:31) Three core skills engineers need to acquire if they want to become effective CEOs. (31:39) “ I used to interview almost everyone until we were at about, you know, 170-180.” (33:82) How creating a 10-year strategy informed their day-to-day decision making. (36:27) The one question he’d have to ask the CEO in an interview before he could accept an offer. LINKS Acceldata Rohit Choudhary, co-founder/CEO Ashwin Rajeeva, co-founder/CTO Gaurav Nagar, co-founder/Senior Architect Raghu Mitra Kandikonda, co-founder/Director of Engineering Lightspeed Venture Partners Acceldata Announces $50 Million in Series C Funding to Expand Market Leadership and Product Innovation in Data Observability (press release) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Startups face unexpected risks every day — cyberattacks, lawsuits, market shifts —but many entrepreneurs don’t think about risk management until it’s too late. In this episode of Fund/Build/Scale, Vouch co-founder/CEO Sam Hodges explains why risk management should be top of mind for early-stage founders. We discuss: Why risk management matters for early-stage startups How Vouch validated, built, and launched Corix as a new business unit The biggest mistakes founders make when managing risk Why work-life balance is a myth for startup leaders Key insurtech trends that early-stage founders should watch in 2025 Sam also shares insights on team structuring, branding, and time management—plus the one question he’d ask an insurtech CEO before taking a job. RUNTIME: 44:36 EPISODE BREAKDOWN (2:27) “ Risk management is something that a lot of founders don't think about a lot, but when it matters, it really matters.” (3:26) How Sam connected with co-founder Travis Hedge. (5:53) Why Vouch’s first team member was a design lead. (6:35) What sets Corix apart from Vouch’s core offerings. (9:05) The process behind starting up a new business unit. (12:42) “ At some point in scale, almost every company is going to organize around products, geographies, or market segments.” (15:05) “ There are three very specific stakeholder groups that we talk to all the time.” (16:26) How the team balanced quantitative metrics against qualitative insights while planning. (18:50) Inside their messaging, branding and rollout strategy for Corix. (21:59) “ The roots of Corix are ‘core’ and ‘risk,’ and we really do think that's what this is all about.” (25:47) How Sam’s day-to-day work is different since launching a new BU. (28:25) A few thoughts about time management and self-care. (30:32) “ I am not a big fan of the term ‘work-life balance.’” (33:22) “ When you make a decision like this, it is going to always feel like it is too early or too late.” (35:48) Insurtech trends early-stage founders should look out for in 2025. (40:14) The biggest risk-management mistakes Sam sees founders making. (43:14) The one question he’d have to ask an insurtech CEO if he were interviewing for a job. LINKS Vouch Sam Hodges, co-founder/CEO Travis Hedge, co-founder/CRO Introducing Corix: An MGA from Vouch, Empowering Brokers with Tailored Insurance Products (PR Newswire) SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.

Amr Awadallah is the CEO and co-founder of Vectara. Previously, he co-founded Cloudera, which went public in 2017 and was acquired for $5.3 billion, and also served as VP of Developer Relations at Google Cloud. His first startup, Aptivia, was acquired by Yahoo, where he later became VP of Product Intelligence Engineering. I talked to him about his experience as an immigrant in Silicon Valley, the frameworks he’s built to articulate vision and credibility, and what he’s learned about pitching investors and recruiting top talent over the years. Runtime: 52:43 EPISODE BREAKDOWN (3:39) “ The more technical definition of what we do is ‘RAG as a service.’” (5:38) ”You ask your car, ‘why is this icon showing, what's wrong with you?’ And the car will tell you, hey, you need to go change my oil.’” (8:07) What makes Vectara a blue-ocean company. (10:05) How to win an investor’s confidence when your current TAM is zero. (12:04) ”There's three things anybody looks for when they're going to join any job, and you need to at least win two of the three.” (15:06) How Amr connected with the other Vectara co-founders. (17:24) Why he’s “a very big opponent to building in stealth.” (21:50) Attending Stanford helped Amr visualize himself as an entrepreneur. (24:34) “ Many entrepreneurs think that the idea is what's going to make a company succeed or not.” (28:54) How he cultivated an appetite for risk again after spending eight years at Yahoo. (32:44) “ Only get the PhD in one case, and one case only: if you want to be a professor.” (37:35) “ By definition, more immigrants will be more willing to take risks.” (41:33) “ There's so many VCs out there pretending they're amazing.” (43:54) There are two types of salespeople: “coin operators” and “innovators.” (48:20) You can start up outside Silicon Valley, but “ if you can move here, move here.” (50:27) Two questions he’d ask the CEO if he were interviewing for a job with a new startup. LINKS Amr Awadallah Vectara Cloudera Google Cloud SUBSCRIBE LinkedIn Substack Instagram Thanks for listening! – Walter.